Free Shemale Stories

Fuck Talk with Melanie Jackson (A talk show transcripy)

THIS IS AN ORIGINAL TRANSCRIPT OF THE PROGRAM “FUCK TALK W/ MELANIE JACKSON” DATED MARCH 10TH 20__ MUSIC CUES ANNOUNCER: Hey everybody! Welcome to “Fuck Talk” with Melanie Jackson”! The show that talks about, you guessed it! FUCKING! Any kind of fucking! Straight fucking! Gay fucking! Any kin... read more

bennyx709 August 28, 2018 100%

Making A Man Out Of Tommy

I have two good friends, Brad and Matt who are actually my fuck buddies. Both of them travel for work, so they tend to be gone a couple of months at a time. I have a key to their apartment, so I can let myself in for sex when they are home and to bring in the mail when they are not. I also get to us... read more

pennypenny August 31, 2018 96%

Too Much Hospitality

Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned t-shirt and some ... read more

ASSEaster5678 September 17, 2018 80%

When Fantasy Comes True 2

After my first threesome encounter with Jenni and her friend, getting a golden shower from three trans women was a bonus. Being drunk and now four of us snuggled in bed, i thought the night had ended but i did hope for more. I was not disappointed as Jenni's friend (Sasha) who had been sleeping d... read more

Sara Banks October 22, 2018 98%

My first time with a man

I have been dressing on and off for many years. But one time when I was feeling more like a woman I decided to join a site where I could meet men who liked girls like me. I met a wonderful man and we constantly kept in touch with each other since he lived in another state. Well he told me that he wa... read more

AndreaPeters October 24, 2018 75%

Lover Delight

Lover's Delight Ebony was a delight for Brian… and Lovers Delight is what the guys called Ebony down at the local. She was a hot babe that everyone wanted but Brian was the one she chose as her full time lover and friend. She knew how to please him and he knew how to tease her and what ... read more

iluvgurls November 14, 2018 80%

HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH

It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... read more

CDDIXIE4U January 8, 2019 100%

MY Party Favor Fantasy

My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... read more

pennypenny January 8, 2019 92%

My 1st Time was Not the Only Time.

One late night after hitting the slopes and partying I left my friends birthday party feeling extra horny. It was about 6 or 7 in the morning now and after having no luck finding an escort I responded to an ad on craigslist posted by a trans woman. I figured two things, this dick isn't going to suck... read more

LesFuax February 16, 2019 100%

The Girl Next Door Ch. 03 by derezzed ©

Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... read more

StevelovesTgirls June 11, 2019 100%

Picked up while on the street and then fucked

I was staying at a women's shelter and the plumbing went to sh**, the place flooded and I was out walking for hours, trying to get WiFi on my laptop in order to contact a friend through Facebook and get them to pick me up, I walked everywhere and in doing so, someone approached me on the street, ... read more

-- TS Lynn Monroe -- July 3, 2019 77%

Porn site meeting and fucking ;)

We started talking on a site. I knew you were for real when you sent me a message introducing yourself. We only spoke for 2 days before we decided to meet up and I was excited to play with a real little slut. You told me the only things off limit were anal and scat otherwise i could do what I wanted... read more

BalkanLoco91Ri August 26, 2019 77%

My Way... Mein Weg... Teil (2)

My Way... Mein Weg... Teil (2) oder wie ich nach 10 Jahren Ehe lernte was ich wirklich will... Da war ich nun. Mit meinem Kopf zwischen den Beinen eines Mannes, und seinen Schwanz im Mund. Genüsslich wie einen Lolli lutsche ich Peters Eichel. Immer tiefer saugte ich seinen Schwanz ein. "Du ... read more

BigBangSlut December 4, 2019 16%

First Time: How I Love Cock

The first time I ever sucked a dick was when I was around 12 years old. I was at a sleep over with a friend. We were camped out in his backyard in a tent and he started things out tentatively by asking about my luck with the ladies, which was non-existent. Then he suggested that since neither of us ... read more

wickeddogg December 11, 2019 83%

Loving Strangers

In the past I had never failed to disclose my sexuality to a new male prospect. I looked good in my tight dress that showcased my woman's ass, and the spike heels that made me look so fuckable. I knew from past experience that guys could get really pissed and violent when they found out you weren't... read more

Regina10 June 23, 2020 85%

Hot Slutty Sissy

Hello, It’s me, and. I am about to make a big decision and right now I am dedicated to my fantasy. I got a call today from one of my ex boyfriends. I got so horny when I heard his voice that my nipples turn to steel. My titties seem to respond to the sound of his vibrating baritone. I couldn’t refu... read more

Regina10 August 14, 2020 91%

My suit fantasy fulfilled

I've always had a thing for a man in a suit, a really smart suit. Maybe it's a secretary fantasy or something, but I just think every man looks sexy in a suit. So it was with great delight that upon making contact with a guy on Grindr a few weeks back, is profile pic showed him in a suit. While t... read more

hornywilla September 14, 2020 100%

Marta, Marta, Marta...

Marta, my good female friend I get to eat my wife out once in a while, was curious about my Brianne side and I told her that I would dress up for her if she would fuck me with a strap on. I don't even think I had gotten out that whole sentence when she said ,"Sure!" You have to understand, this is o... read more

smtmsbrianne September 15, 2020 100%

First time with ladyboy / bottom

Hi everyone! now it is my turn to share my experience in Thailand. We were on a Christmas vacation on an island, and I didn’t even know ladyboy existed then. At a Christmas beach party I chatted and danced with a woman and we ended up in my bungalow. We kissed a lot and I knew that now I was g... read more

FoxyLover'ts October 6, 2020 81%

My first sexual experience with a man

My first time having sex with a man, learning to be a girl that I felt inside. I was 20 years old, just moved to the UK, with my wife at the time as I was stationed at one of the bases there. I had been dressing up and wearing panties and stockings and bras mostly up till that time. I had a coupl... read more

Mistysis October 19, 2020 100%